The company's offerings encompass a network of podcasts; a news and opinion website; live shows and tours; and a social media and live streaming presence. It aims to foster open conversation between liberals and support grassroots activism and political participation.

The company's flagship podcast, Pod Save America, airs twice weekly and averages more than 1.5 million listeners an episode. By November of its first year, the podcast had been downloaded over 120 million times.[2]

After Donald Trump's victory in the 2016 Presidential Election, Favreau, Lovett and Vietor decided they wanted to do podcasting and activism on a full-time basis. In an interview with Recode's Kara Swisher, Vietor explained that “If Hillary had won, we probably would’ve kept doing this as a hobby... But when she lost, I think we all had this existential crisis, where it didn’t feel right to wake up every day and obsess about politics and what’s happening in the country, and then go to work doing something else.”[3]

The quartet ended Keepin' it 1600 in December 2016. Favreau, Lovett and Vietor formed their own company, Crooked Media, and, the following month, launched a new podcast called Pod Save America.[5] Pfeiffer opted not to join the company, and instead co-host the Thursday edition of the show.[6]

Crooked Media is named after a favorite term used by President Trump. When asked whether he thought Crooked Media was a 'media company', Favreau said, “I don’t know if it’s a political movement or a media company.”[7]

The company announced a major expansion in October 2017 with the launch of Crooked.com, a text journalism site helmed by Editor-In-Chief Brian Beutler, a former New Republic senior editor. The expansion introduced the 'Crooked Contributors' network - a diverse group of journalists, activists, organizers, policy experts, campaign veterans and comedians who will be featured in podcasts, videos, and articles produced by the company.[8]

The company is not raising money from outside investors; instead using advertising revenue to fund the business.[3]

Hosted by organizer and activist DeRay Mckesson,[11][12]Pod Save the People talks about culture, social justice, and politics by exploring the history, the language, and the people who are shaping the struggle for progress — and talking about the steps that each individual can take to make a difference.[13]

Hosted by Vietor, a former national security council spokesman in the Obama administration. Pod Save the World attempts to discuss foreign policy and international relations in a relatable and down to earth way. The show brings listeners behind the scenes into White House Situation Room meetings and secret negotiations through a series of conversations with people who were there. The podcast also focuses on what listeners can do to make an impact on global events.[14]

Hosted by Lovett, former speech and joke writer for President Obama. Lovett or Leave it is a recording of a weekly live show and features the eponymous host dissecting the news with a panel of guests. The show features a variety of games, as well as one-on-one interviews that center around the week's news and American politics.[15]

Hosted by political journalist Ana Marie Cox. With Friends Like These delves into social, cultural, and, to a lesser extent, political issues through in-depth interviews. Namely, how to bridge divides in our society and approach through conversations with peers. Cox focuses on attempting to have difficult conversations in a public space.[16]

Crooked Media embarked on its first tour, Pod Tours America, in fall of 2017. The tour featured live versions of Pod Save America and Lovett or Leave it, and appearances from Mckesson, Cox, various members of the 'Crooked Contributors' network, and special guests.[20] Live shows are recorded and released as podcasts.

A second tour, Pod Tours the World, was announced for 2018, with live shows in Stockholm, Oslo, Amsterdam and London.[21]

Unlike more traditional media organisations, Crooked Media engages directly in political activism, including advocating for policies and candidates, supporting get out the vote efforts, raising money, and driving phone calls and demonstrations.[2]

During its first year, it partnered with progressive advocacy group MoveOn to send nearly 2,000 Pod Save America listeners to Republican town-hall meetings, with Swing Left to raise over a million dollars for challengers to House Republicans in the 2018 midterm elections, and with Indivisible to drive phone calls in favour of the Affordable Care Act. In the 2017 Virginia elections, the company lent its support to Democratic candidates across the ballot, including Lt. Gov. Ralph Northam in the state's governor race.[2]

Towards the end of 2017, the company launched 'The Crooked 7' in partnership with Swing Left, a new initiative to raise money to flip seven California House districts held by Republicans in the 2018 midterm elections.[22]

The company's podcasts regularly sit near the top of the iTunes list of most popular podcasts.[7] The New York Times has called Crooked Media 'the left’s answer to conservative talk radio'.[2]Pod Save America was called 'the nation’s most popular political podcast' by Newsweek.[23] Reviewing the first episodes of the company's flagship podcast, The Guardian noted: "Pod Save America's commentators are sparky and funny – and they have a habit of talking a whole lot of sense."[24]